President Barack Hussein Obama came to Chicago last Friday to give a speech at Hyde Park Academy on the South Side, and I went to write about it.

Technically, this was my third time seeing the president speak live after making it to election night rallies in both ’08 and ‘12, but during this speech I would not have to fight the teeming hordes of Obamabots, which can consist of the sharp elbows of old Jewish ladies, 400-pound linebacker-looking dudes in FUBU hats stepping on your feet, or bubbly crowds that seemingly fell off the pages of the blog Stuff White People Like. I had a press pass to this sucker, which meant I could journalist my way all the hell over the place, and if I had a problem with the Wi-Fi there’d be some young, pert, blonde woman to address my concerns.

Just west of Lake Michigan, Hyde Park Academy is nestled between Jackson Park, a bit of low-income housing, and the University of Chicago campus. It’s basically 63rd Street, which, if you’re familiar with the geography of Chicago homicides, lies just outside the belt of the city’s most intractable violence. I don’t get down to Hyde Park much, but I’ve been enough that I know at least a few good secret streets for parking, so I stashed my car a decent walk away from HPA in hopes of beating motorcade traffic afterward and made my way to the school.

This was a very typical white-guy-on-the-South-Side stroll in that I got a few fantastically curious looks and one tall, unintelligible gentleman, who stopped to mumble something at me. I listened to him long enough to understand that he was either drunk or schizophrenic and we both agreed to move on amicably.

The underlying lesson of this moment having to do very much with Obama’s speech that day: to be very blunt about it, there are a lot of legitimately fucked up cities in the United States, and a core part of their fucked-upedness has to do with those cities segregated legacies. Chicago has become a particular exemplar recently with homicides at their highest level since 1997. Awash in cheap handguns and battered, struggling schools, with unemployment and incarceration the norm in some neighborhoods, Chicago saw 730 homicides in 2012.

Not in my part of town, though. I’m a northsider, so those neighborhoods might as well be a separate city. And therein lies part of the problem.

Security preparations for HPA were borderline militarized. A row of CTA busses lined the street in front of the school in a makeshift barricade, and each end of the street had two snowplows on either side of a cop car with their snouts menacingly lowered as if braced for Kabul suicide drivers. After getting redirected around multiple obstacles by Chicago PD, I finally spotted the other white guys in ties, their doughy backfat visible through winter coats—this is how you recognize fellow journalists.

Following a credentialing, bag search, and full-body wand, I made my way to the school’s gymnasium where bleachers and cameras surrounded a single podium, and the treacly sky-blue on the cinderblock somehow called to mind every high school gymnasium from San Diego to Portland, Maine.

I had a lot of time to kill, which I spent reading a book and chatting with the young, pert blonde woman in charge of press advance named Megan. Megan’s job was to get to everywhere the president was speaking a week in advance and set up, well, everything. She ate as she walked around trouble-shooting the crappy internet, and I tried to imagine how she ever maintained a personal life or had time to get laid. During the campaign, I pointed out, Obama was doing one of these events every five minutes.

“I’ve seen a lotta high school gyms,” she explained, and then we talked about Ohio, where her staff and Romney’s staff were basically high-fiving as they breezed by each other on the highways.

When our mayor finally emerged to introduce Obama, I was really feeling for the unfortunate kids who’d been standing on the rafters behind the podium for well over an hour. I imagined the ache in their legs, the way they would have to shift their weight around just to keep the blood circulating. It reminded me of every middle school choir concert I’d ever suffered through as a participant.

Rahm Emanuel’s nasty, F-bomb-slanging reputation aside, he’s one diminutive dude. His reedy voice bounced around the gym, and he wasted no time introducing Obama, possibly because you could feel the crowd leaning in as it attempted to anticipate which sentence would lead to the president walking on-stage.

It was a veritable who’s who of Chicago political influence. Senator Dick Durbin, Governor Pat Quinn, Congressman Bobby Rush, Attorney General Lisa Madigan, and just about every relevant clergy member in the state. On the side opposite the journos, HPA students sat, uniformed and bottled up, slapping at each other’s hands even as they all seemed to hold on and link arms the way a March Madness Cinderella will when a victory looks within reach through a couple of free throws.

When Rahm finally gave his welcome and Obama strode out from behind the curtain erected over the back of the gym, the crowd went absolutely ballistic. Every last student was on his or her feet, just shrieking like Justin Bieber fans. Camera phones rose in unison to touch-pad pics or start video recordings. Obama—typically magnificent grin beaming in every direction—jogged up to the podium, waving. I seriously thought some of those kids might faint, and it reminded me that for all the haughty blather on cable news shows and op-ed pages, it wasn’t rocket science to understand that Obama’s presidency meant something real to kids who’d previously only studied white men and slave-owners as American executives.

“Everybody have a seat. Y’all relax,” said Obama as he took to the mic. “It’s just me.”

Obama was surrounded by a preposterous number of Secret Service agents, all facing every angle of the crowd. Several more patrolled the gym and stood guard by the doorways. Some of these people looked semi-normal, and earlier, when a young lady stopped me at the door to ask that I display my press pass I almost thought she was a student kidding around with me. Then again, some of them looked straight out of central casting: hard, ex-Navy Seal-looking types wearing suits two of me could have fit into (Also how are they still using the little earpiece with the coiled wire running into the suit? Can’t we update that in the age of the Bluetooth? I feel like Jack Bauer always had some kind of way less cumbersome two-way com.) It made you wonder what kind of eventualities they were prepared for—like if the entire crowd suddenly got the 28 Days Later virus and rushed the stage, were they ready for that?

Such amusing thoughts were on my mind as Obama launched into the boiler-plate of his speech. He was from here, he reminded the crowd. Taught around the corner at the University of Chicago, organized in the neighborhoods to the south, met Michelle here, knew half the people in the crowd. This last one in particular struck me because throughout his speech, you could see Obama giving little nods, winks, and acknowledgments to practically everyone in the first five rows. Beyond that, I was situated directly in front of one of the two teleprompters, so whenever he read from that side it felt like he was making eye contact with me.

I probably started blushing.

(Truth be told, I’d thought long and hard about what I’d ask him if the chance should have miraculously arisen. While I like to believe it would be something hard-hitting like, “How can you reconcile pleading with the public about gun violence when you’ve overseen military campaigns that have unleashed brutal violence on communities of impoverished people overseas without any kind of accountability?” I would probably end up asking something like, “Ohmygod will you and Michelle adopt me? And then can we play basketball together? I’ll run the point, you play the two or the three?”)

His speech, for the most part, was a reiteration of the previous week’s State of the Union. He repeated that night’s most powerful moment when he said of those families victimized by guns, “They deserve a vote.” Leave it to the one of the best speakers of the era to come up with the perfect Twitter hash-tagable line to bully his Republican opponents into an awkward corner. As he pointed out, the U.S. is in a situation where we have the equivalent of a Newtown massacre every four months. Slate has created an excellent catalogue of the gun deaths since Newtown in which you can scroll over every individual body, demarcated by bathroom stall figures of various sizes, depending on whether they were an adult, teenager or child. If you click on one, you can get the entire story: children shooting themselves in the face, husbands murdering their wives, random teenagers gunned down in the street. One of those figures is Hadiya Pendleton, the fifteen year old murdered in a South Side park weeks after attending the inauguration. Her parents, who’d sat with the First Lady at the State of the Union, were in the crowd and received a roaring applause when Obama spoke of their particular, but not unusual, tragedy.

There’s not enough space/ bytes/ ink or whatever here to give proper reflection to just how weird American gun culture has become, but the staunch, bipartisan resistance to Obama’s proposals has given rise to an even more virulent, bizarre group of conspiracy theorists who think the government stages mass shootings as a pretense to take away all guns. Even Bruce Willis, while promoting “A Good Day to Die Hard,” came out for the wacky-enough idea that universal background checks or assault weapons band or limits for magazine size somehow constitutes an assault on the Bill of Rights.

All this reduces the president to merely asking Congress to put his most basic, common sense ideas to a vote—a vote they will surely not have the courage to take.

The speech went far beyond guns, though, and included ideas for a new public housing initiative, his pitch for quasi-universal pre-school, and a raise in the minimum wage. The last one got a very robust cheer. There are a lot of rooms in the country where no one knows a person making minimum wage, but this was not one of those rooms. News rooms, yes. CNN offices, sure. Production companies that make TV shows, obviously. So it’s only almost “all the media we consume ever” that ignores the question of how much does it suck to try to provide for oneself, let alone a family, on the minimum wage?

Obama was at his best, however, when he wandered off-script and began talking about the kids he’d met from a program called BAM (Becoming a Man). He explained how he’d had his own issues growing up, but his environment—one of relative privilege in Hawaii, at least compared to these kids—had been more forgiving.

"So when I screwed up, the consequences weren't as high as when kids on the South Side screw up," he said. "So I had more of a safety net. But these guys are no different than me, and we had that conversation about what does it take to change."

He spoke of the role of parents, saying, “that includes gay or straight parents,” which received a surprisingly robust cheer from even the student section (which is something that should not be overlooked: the kind of impact Obama will have on normalizing homosexuality for the next generation).

He ended with a familiar rhetorical flourish, speaking of how hard it is to change the way things are, but if you can change a room, then you can change a neighborhood, and if you can change a neighborhood, you can change a city, and so forth. The speech was a laundry list of ways to address the woes that plague black (and increasingly, white) communities in American cities. For all the inspiration Obama lends as the first black president, he’s been hamstrung by his race as well, ever leery that conservative media loves and cannot help but tie his safety net-building policies to his race and frame his entire presidency as a big socialist scheme to take white people’s money and give it to poor, lazy black people. If you’re Cornell West this is unforgivable, but maybe if you’re Barack Obama it’s simply the reality of political life as the first black president.

During his first term, he signed a bill that reduced the disparity between sentencing for crack and powder cocaine. This was not not a big deal. The previous sentencing disparity was about 100 to 1, and the bill Obama signed reduced it to roughly 18 to 1. Yet there was no public signing ceremony. It was all done behind closed doors and out of the spotlight. Why? Because the sentencing disparity is almost entirely about race. Black people get predominantly arrested for crack, white people for cocaine. This wasn’t an end to the insane war on drugs, but it constituted a major step in the right direction that went almost unnoticed and is now totally forgotten.

Yet the story of these sentencing standards is apocryphal, and as Obama wrapped up his speech and the crowd again erupted, I was left wondering what everyone in the room thought of all this. What did the Hyde Park Academy students think? What did Megan the advance press coordinator think? What did all these bored journalists regurgitating White House talking points and conventional wisdom think? We know what BAM counselor Marshaun Bacon thought because he told the Tribune:

"When you can have an informal and candid conversation with the president of the United States and he tells you that he wishes he had grown up with his father, that makes a difference."

And seeing Obama that close, hearing the familiar timbre of his voice, and listening to him describe with that fantastic, near-delusional optimism that defines his outlook that there is not only reason but a responsibility to hope, to believe in his favorite quote of Dr. King’s, that “the arch of the moral universe is long but it bends toward justice,” it was difficult to not feel just as giddy as those students in the bleachers.

Yet it’s easy to talk like this. Well, maybe not easy—no one does it quite as well as Obama. But it’s easy enough. What’s harder is to change everything that’s below the surface of neighborhoods like Englewood and Roseland and Flint, Michigan, and Over-the-Rhine in Cincinnati and pockets of Jacksonville and Dallas and Harlem and Baltimore and Detroit and Cleveland and endless other communities. What’s harder is to change the institutional underpinnings of a system designed to profit when kids in the BAM program fail.

Because conservatives will rail against “handouts” and “welfare” and anything that even smells of redistribution, but what they don’t acknowledge is that we already have social policy in the U.S. It’s called prison, and it’s way more expensive than if simply we enacted everything on Obama’s wish list. We lock up a larger percent of our population than any country on earth: with 5 percent of the world’s population, we jail 23 percent of its prisoners. Because prisons are big money, and it’s not just hefty sentences for non-violent drug offenders that are the problem. The prison-industrial complex (not to mention gun manufacturers) benefits from failing schools in the South Side neighborhoods that exist as the remnants of racial isolationist policy (The placement of the Dan Ryan highway was famously a decision about isolating black neighborhoods on the South Side) And what else are the Chicago suburbs but a method white parents took to isolate their children in an education system they (rightly) saw as winner-take-all? Chicago public schools aren’t struggling because the teachers aren’t working hard enough but because the resources, small class sizes, and opportunities have been horded for an increasingly smaller segment of society. Segregated schools are de facto public policy, and there are almost no “education reformers” who want to touch the things we’d have to do to actually fix that. But hey, uneducated kids make great customers for prisons, which can put them to work for sub-minimal wages, turning out an even larger profit. And here I’m just rambling about the most totally obvious aspects of a broken system that’s purposefully broken. We won’t even get into the predatory hunger of payday lenders, the old subprime mortgage racket, auto title loans, credit cards, rent-to-own schemes, for-profit colleges and all the other myriad ways businesses have come to turn a fat dollar by ripping off the working poor. Neighborhoods plagued by violence and dysfunction have a value to the capitalistic treadmill, whether it’s the Marlo Stanfields or the bankers at Goldman Sachs.

It’s not that I don’t think Barack Obama doesn’t understand all this—it’s that when you think about the obstacles, influences, money and power running under the chaos of places like the South and West Sides Chicago, it’s difficult not to find yourself cynical.

After the speech, while walking back to my car, I stopped at a crosswalk beside a classic little old lady with gray-brown skin and a splash of dark freckles. She barely came up to my chest, and she had to bend her entire back to crane up at me, likely taking in my skin color and tie the same way every American takes in everyone’s skin color and dress attire.

“Oh, did you see the Obamas?” she asked, smiling.

“Saw one of ‘em,” I told her.

“Was Michelle and the girls there? I thought Michelle and the girls were coming, too.”

“No, it was just him.”

“Oh, that’s too bad, I love those girls. So beautiful. Was he good?”

“Well, I’m supposed to be objective about that kind of thing—you know, a supposed journalist and all. But yes, he was pretty good.”

“I always said, the three best days of my life was when I was married, when my three babies were born, and when I met Barack—but he was just a state senator then.”

“Wait, your three kids only get one day?” I kidded her.

She flipped her hand at the notion. “I couldn’t make ‘em different days because they’d all get in a argument about which day was the better one.”

I smiled. The crosswalk light changed, and I slowed to walk across with her. The cop directing traffic yelled at some kids who went sprinting into the street as traffic tried to get started.

“So you met Obama?” I asked.

“Just shook his hand at some meet-your-senator thing he was doing. But I couldn’t believe everything else that happened to him. I told my friend at the time, we just thought he was so handsome!” She laughed really hard at this in that way that old ladies do, with pockets of sinus juices vibrating.

I asked her if I could interview her quickly, and she declined. I asked her if I could at least quote her, and she said no. So I thanked her anyway and began to walk away, at which point she called back to me, “How ‘bout this?” she said. “God bless that man. God bless him. God bless. God bless him.”

And then she continued on her way.

Only a few hours after fourteen-year-old Destini Warren stood behind Obama listening to his speech—one of the kids whose tired legs I worried for while we all waited for the president to appear—she discovered her older sister had been shot and killed in North Chicago. Janay Mcfarlane was eighteen and the new mother of a three-month old son.